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Check prices for these dates

Tonight
3 Sep - 4 Sep
Tomorrow
4 Sep - 5 Sep
This weekend
5 Sep - 7 Sep
Next weekend
12 Sep - 14 Sep

Top Holiday Rentals in Countryside

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (905)
"great food spots all around and beautiful sites to see "
The price is ฿4,367
฿6,074 total
includes taxes & fees
4 Sept - 5 Sept
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (491)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (347)
"A lot of good food options walkable distance. "
The price is ฿8,969
฿11,251 total
includes taxes & fees
4 Sept - 5 Sept
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (354)
"Great stay!"
The price is ฿5,784
฿6,789 total
includes taxes & fees
4 Sept - 5 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (641)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is ฿6,403
฿7,516 total
includes taxes & fees
22 Sept - 23 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (194)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (209)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is ฿6,293
฿7,387 total
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (337)
"Easy parking. Close to El. Nice condo."
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is ฿5,468
฿6,419 total
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is ฿5,784
฿6,789 total
includes taxes & fees
4 Sept - 5 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (19)
"Excellent location and very clean! Would stay again!"
The price is ฿2,357
฿4,383 total
includes taxes & fees
4 Sept - 5 Sept
Wrigleyville Suites
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (166)
"This place has everything for a multi-night stay."
Kasa River North Chicago
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (58)
"Good "
The price is ฿2,734
฿3,088 total
includes taxes & fees
10 Sept - 11 Sept
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (134)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is ฿6,595
฿7,742 total
includes taxes & fees
14 Sept - 15 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is ฿24,233
฿40,079 total
includes taxes & fees
8 Sept - 9 Sept
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is ฿6,842
฿8,032 total
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (17)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is ฿3,451
฿6,388 total
includes taxes & fees
15 Sept - 16 Sept
Ground Floor Studios in Chicago by 747 Lofts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Countryside Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"I enjoyed my stay here "
Carmen 1-night trip
Posted 10 days ago
The Allegro Royal Sonesta Hotel Chicago Loop

Find out more about Countryside

Find out more about Countryside

Search for holiday rentals in Countryside on Expedia! You can easily find your home rentals, villas, holiday apartments in Countryside using one of the methods below:

  • View our selection of featured holiday rentals in Countryside
  • Use the map to find apartments and other holiday homes in the Countryside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Countryside while they last

Look no further and take a look at our great range of rental properties in Countryside!

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Frequently asked questions

Can I find holiday rentals in Countryside?

Yes, there are holiday rentals close to the most popular sights in Countryside, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Countryside. Make sure you have time to check out the live music and zoo during your trip.

What can I see and do in Countryside?

Explore the area and family-friendly sights such as Parkway Bank Park Entertainment District, or get out into nature at a spot like Millennium Park. In the wider area, you’ll find popular places such as Michigan Avenue and Navy Pier.

What are holiday rentals like in Countryside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Countryside. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for small groups.